HU203764B - Process for producing 11-beta-4,9,15-estratiene derivatives and pharamceutical compositions containing them - Google Patents

Process for producing 11-beta-4,9,15-estratiene derivatives and pharamceutical compositions containing them Download PDF

Info

Publication number: HU203764B
Authority: HU; Hungary
Prior art keywords: group; compound; formula; compounds; hydroxy
Prior art date: 1987-07-16

Application number

HU884582A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT52112A (en

Inventor

Echkhard Ottow

Helmut Hofmeister

Stefan Scholz

Guenter Neef

Walter Elger

Sybille Beier

Chwalisz Krzysztof De

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-07-16

Filing date

1988-07-15

Publication date

1991-09-30

1988-07-15 Application filed by Schering Ag filed Critical Schering Ag

1990-06-28 Publication of HUT52112A publication Critical patent/HUT52112A/hu

1991-09-30 Publication of HU203764B publication Critical patent/HU203764B/hu

Links

238000000034 method Methods 0.000 title claims description 7
239000000203 mixture Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 67
-1 hydroxyimino Chemical group 0.000 claims abstract description 40
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
125000002252 acyl group Chemical group 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000468 ketone group Chemical group 0.000 claims description 5
238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
239000012445 acidic reagent Substances 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
125000002355 alkine group Chemical group 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
238000003776 cleavage reaction Methods 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 25
229910052739 hydrogen Inorganic materials 0.000 abstract description 4
239000000460 chlorine Substances 0.000 abstract description 3
125000004432 carbon atom Chemical group C* 0.000 abstract 4
125000000217 alkyl group Chemical group 0.000 abstract 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
125000005041 acyloxyalkyl group Chemical group 0.000 abstract 1
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230000000380 anti-gestagenic effect Effects 0.000 abstract 1
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229910052731 fluorine Inorganic materials 0.000 abstract 1
239000011737 fluorine Substances 0.000 abstract 1
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125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
229910052740 iodine Inorganic materials 0.000 abstract 1
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NRUBUZBAZRTHHX-UHFFFAOYSA-N lithium;propan-2-ylazanide Chemical compound [Li+].CC(C)[NH-] NRUBUZBAZRTHHX-UHFFFAOYSA-N 0.000 description 1
230000007774 longterm Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000013011 mating Effects 0.000 description 1
230000005906 menstruation Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
201000009395 primary hyperaldosteronism Diseases 0.000 description 1
102000003998 progesterone receptors Human genes 0.000 description 1
108090000468 progesterone receptors Proteins 0.000 description 1
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

HU884582A 1987-07-16 1988-07-15 Process for producing 11-beta-4,9,15-estratiene derivatives and pharamceutical compositions containing them HU203764B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873723788 DE3723788A1 (de)	1987-07-16	1987-07-16	11(beta)-phenyl-4,9,15-estratriene, deren herstellung und diese enthaltende pharmazeutische praeparate

Publications (2)

Publication Number	Publication Date
HUT52112A HUT52112A (en)	1990-06-28
HU203764B true HU203764B (en)	1991-09-30

Family

ID=6331846

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU884582A HU203764B (en)	1987-07-16	1988-07-15	Process for producing 11-beta-4,9,15-estratiene derivatives and pharamceutical compositions containing them

Country Status (12)

Country	Link
US (1)	US5132299A (de)
EP (1)	EP0299913B1 (de)
JP (1)	JP2792876B2 (de)
AT (1)	ATE87631T1 (de)
CA (1)	CA1320946C (de)
DD (1)	DD281809A5 (de)
DE (2)	DE3723788A1 (de)
DK (1)	DK43189A (de)
ES (1)	ES2054859T3 (de)
FI (1)	FI94349C (de)
HU (1)	HU203764B (de)
WO (1)	WO1989000578A1 (de)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3917274A1 (de) *	1989-05-24	1990-11-29	Schering Ag	9(alpha)-hydroxy-19, 11(beta)-ueberbrueckte steroide, deren herstellung und diese enthaltende pharmazeutische praeparate
DE59010853D1 (de) *	1989-08-04	1998-12-03	Schering Ag	11 Beta-Aryl-gona-4,9-dien-3-one
DE4042004A1 (de) *	1990-12-22	1992-06-25	Schering Ag	14(beta)-h-, 14- u. 15-en-11(beta)-aryl-4-estrene
US5407928A (en) *	1990-08-15	1995-04-18	Schering Aktiengesellschaft	11β-aryl-gona-4,9-dien-3-ones
US5639598A (en) *	1994-05-19	1997-06-17	The Trustees Of The University Of Pennsylvania	Method and kit for identification of antiviral agents capable of abrogating HIV Vpr-Rip-1 binding interactions
US5780220A (en) *	1994-05-19	1998-07-14	Trustees Of The University Of Pennsylvania	Methods and compositions for inhibiting HIV replication
US5767113A (en) *	1995-05-10	1998-06-16	The Salk Institute For Biological Studies	Compounds useful for concurrently activating glucocorticoid-induced response and reducing multidrug resistance
IL118974A (en) *	1995-08-17	2001-09-13	Akzo Nobel Nv	History 11 - (Transformed Phenyl) - Astra - 4, 9 - Diane, their preparation and pharmaceutical preparations containing them
DE19706061A1 (de)	1997-02-07	1998-08-13	Schering Ag	Antigestagen wirksame Steroide mit fluorierter 17alpha-Alkylkette
US6090798A (en) *	1997-12-19	2000-07-18	Alcon Laboratories, Inc.	Treatment of GLC1A glaucoma with glucocorticoid antagonists
DE102004059880A1 (de) *	2004-12-10	2006-06-14	Grünenthal GmbH	Stabiles, hormonhaltiges (Zwischen-)Produkt
WO2011150209A1 (en)	2010-05-26	2011-12-01	Corcept Therapeutics, Inc.	Treatment of muscular dystrophy
AU2016226451B2 (en)	2015-03-02	2019-12-19	Corcept Therapeutics, Inc.	Use of glucocorticoid receptor antagonist and somatostatin analogues to treat ACTH-secreting tumors
US10610534B2 (en)	2015-03-30	2020-04-07	Corcept Therapeutics, Inc.	Use of glucocorticoid receptor antagonists in combination with glucocorticoids to treat adrenal insufficiency
KR20180052120A (ko)	2015-08-13	2018-05-17	코어셉트 쎄라퓨틱스, 잉크.	Acth-의존성 쿠싱 증후군을 감별 진단하는 방법
JP6765443B2 (ja)	2016-01-19	2020-10-07	コーセプトセラピューティクス，インコーポレイテッド	異所性クッシング症候群の鑑別診断
MX2019011543A (es)	2017-03-31	2019-12-16	Corcept Therapeutics Inc	Moduladores del receptor de glucocorticoides para el tratamiento de cancer cervical.
WO2018236749A2 (en)	2017-06-20	2018-12-27	Corcept Therapeutics, Inc.	Methods of treating neuroepithelial tumors using selective glucocorticoid receptor modulators
EP3713086A1 (de)	2019-03-18	2020-09-23	Siemens Aktiengesellschaft	Schutzschaltung für einen halbleiterschalter
JP2024500748A (ja)	2020-12-18	2024-01-10	インスティルバイオ（ユーケイ）リミテッド	腫瘍浸潤リンパ球の処理

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2530817A (en) *	1948-05-19	1950-11-21	Univ Pennsylvania	13-monomethyl steroids
US2940968A (en) *	1958-10-01	1960-06-14	Merck & Co Inc	Dimethylated steroids and processes for producing same
CH558346A (de) *	1971-06-17	1975-01-31	Sandoz Ag	Verfahren zur herstellung neuer 3-oximino-17(alpha)-propadienyl-substituierter steroide.
DE3042529A1 (de) *	1980-11-07	1982-06-24	Schering Ag, 1000 Berlin Und 4619 Bergkamen	11-methylen- (delta)(pfeil hoch)1(pfeil hoch)(pfeil hoch)5(pfeil hoch) -steroide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
FR2522328B1 (fr) *	1982-03-01	1986-02-14	Roussel Uclaf	Nouveaux produits derives de la structure 3-ceto 4,9 19-nor steroides, leur procede de preparation et leur application comme medicaments
EP0116974B1 (de) *	1983-02-18	1986-10-29	Schering Aktiengesellschaft	11-Beta-Aryl-Estradiene, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
DE3347126A1 (de) *	1983-12-22	1985-07-11	Schering AG, 1000 Berlin und 4709 Bergkamen	11ss-aryl-estradiene, deren herstellung und diese enthaltende pharmazeutische praeparate
AU580843B2 (en) *	1985-02-07	1989-02-02	Schering Aktiengesellschaft	11``-phenyl-gonanes, their manufacture and pharmaceutical preparations containing them

1987
- 1987-07-16 DE DE19873723788 patent/DE3723788A1/de not_active Withdrawn
1988
- 1988-07-15 WO PCT/DE1988/000447 patent/WO1989000578A1/de not_active Ceased
- 1988-07-15 HU HU884582A patent/HU203764B/hu not_active IP Right Cessation
- 1988-07-15 JP JP63505988A patent/JP2792876B2/ja not_active Expired - Lifetime
- 1988-07-15 DE DE8888730161T patent/DE3879787D1/de not_active Expired - Fee Related
- 1988-07-15 DD DD88317992A patent/DD281809A5/de not_active IP Right Cessation
- 1988-07-15 EP EP88730161A patent/EP0299913B1/de not_active Expired - Lifetime
- 1988-07-15 ES ES88730161T patent/ES2054859T3/es not_active Expired - Lifetime
- 1988-07-15 AT AT88730161T patent/ATE87631T1/de not_active IP Right Cessation
- 1988-07-15 CA CA000572238A patent/CA1320946C/en not_active Expired - Fee Related
- 1988-07-15 US US07/458,668 patent/US5132299A/en not_active Expired - Fee Related
1989
- 1989-01-31 DK DK043189A patent/DK43189A/da not_active Application Discontinuation
1990
- 1990-01-15 FI FI900217A patent/FI94349C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK43189D0 (da)	1989-01-31
CA1320946C (en)	1993-08-03
EP0299913A1 (de)	1989-01-18
DK43189A (da)	1989-01-31
EP0299913B1 (de)	1993-03-31
JP2792876B2 (ja)	1998-09-03
DE3879787D1 (de)	1993-05-06
JPH03500642A (ja)	1991-02-14
US5132299A (en)	1992-07-21
DD281809A5 (de)	1990-08-22
FI94349C (fi)	1995-08-25
DE3723788A1 (de)	1989-01-26
FI900217A0 (fi)	1990-01-15
FI94349B (fi)	1995-05-15
ATE87631T1 (de)	1993-04-15
HUT52112A (en)	1990-06-28
ES2054859T3 (es)	1994-08-16
WO1989000578A1 (fr)	1989-01-26

Legal Events

Date	Code	Title
1995-04-28	HMM4	Cancellation of final prot. due to non-payment of fee
1995-06-28	HNF4	Restoration of lapsed final prot.
2004-04-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
US4814327A (en)	1989-03-21	11 β-(4-isopropenylphenyl)estra-4,9-dienes, their production, and pharmaceutical preparations containing same
HU203764B (en)	1991-09-30	Process for producing 11-beta-4,9,15-estratiene derivatives and pharamceutical compositions containing them
KR0161975B1 (ko)	1998-11-16	11베타-치환 프로게스테론 유사체
JP4368945B2 (ja)	2009-11-18	新規１９―ノループレグネン誘導体類
HU196825B (en)	1989-01-30	Process for producing 10-substituted steroids and pharmaceutical compositions comprising the same
RU2187510C2 (ru)	2002-08-20	Производные 16-гидрокси-11-(замещенный фенил)-эстра-4,9-диена, соединение, фармацевтическая композиция
PL191808B1 (pl)	2006-07-31	17-α Fluoroalkilowe steroidy, preparaty farmaceutyczne je zawierające oraz ich zastosowanie
JPH0764870B2 (ja)	1995-07-12	１１β‐アリール‐エストラジエン、その製法及びこれを含有する抗ゲスターゲン及び抗糖質コルチコイド製剤
US5843933A (en)	1998-12-01	11β-aryl-4-estrenes, process for their production as well as their use as pharmaceutical agents
JPH0443077B2 (de)	1992-07-15
IE58149B1 (en)	1993-07-14	11 beta-phenyl-gonanes,their manufacture and pharmaceutical preparations containing them
BRPI0718409A2 (pt)	2013-12-17	Antagonistas de receptor de progesterona
JP2010120973A (ja)	2010-06-03	アゴニスト又はアンタゴニストホルモン特性を有する２０−ケト−１１β−アリールステロイドとその誘導体
US4705783A (en)	1987-11-10	9α, 11β-substituted and 11β-substituted estranes
US5093507A (en)	1992-03-03	10β,11β-bridged steroids
IE67514B1 (en)	1996-04-03	11beta-phenyl-14betaH steroids
HUP9903353A2 (hu)	2000-03-28	7Alfa-/5-metil-amino-pentil/-ösztratriének, e vegyületeket tartalmazó gyógyszerkészítmények és ezek alkalmazása gyógyszerek előállítására
CN100354299C (zh)	2007-12-12	在11位带有烃取代基的非芳香族雌激素甾族化合物
JP3181589B2 (ja)	2001-07-03	６、７−変性１１β−アリール−４−エステレン
MXPA99007057A (es)	2000-07-01	Esteroides con actividad antigestagena que tienen una cadena fluorada de 17-alfa-alquilo